2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-cyclopentyl-4-cyclohexyl-7,7-dimethyl-3-(4-trifluoromethylbenzoyl)-7,8-dihydro-6H-quinolin-5-one

HRID 1645319Notes

Reaction equation

HRID 1645319 reaction equation
[CH:1]1([C:6]2[NH:7][C:8]3[CH2:9][C:10]([CH3:36])([CH3:35])[CH2:11][C:12](=[O:34])[C:13]=3[CH:14]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:15]=2[C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[CH:1]1([C:6]2[C:15]([C:16](=[O:27])[C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=3)=[C:14]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:13]3[C:12](=[O:34])[CH2:11][C:10]([CH3:36])([CH3:35])[CH2:9][C:8]=3[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 154031502-cyclopentyl-4-cyclohexyl-7,7-dimethyl-3-(4-trifluoromethylbenzoyl)-4,6,7,8-tetrahydro-1H-quinolin-5-one

Product 1

HCID 98272012-cyclopentyl-4-cyclohexyl-7,7-dimethyl-3-(4-trifluoromethylbenzoyl)-7,8-dihydro-6H-quinolin-5-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.13 g (6.3 mmol) of the compound from Example 1A are dissolved in 64 ml of dichloromethane, and 1.42 g (6.3 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) are added a little at a time at 0° C. With stirring, the mixture is warmed to room temperature over a period of 3 h. The mixture is concentrated on a rotary evaporator and the residue is purified by chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 5:1).

Workup

  1. concentrationThe mixture is concentrated on a rotary evaporator
  2. customthe residue is purified by chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-d06b4c66f6be43678de71ef85eea3c82
Source dataset
uspto-grants-2012_02
Patent number
US08124775B2

Reaction notes

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